1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 89835594, compound

HRID 2277095Notes

Reaction equation

HRID 2277095 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][C@H:19]3[C:24](O)=[O:25])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[C:48]([O:52][C:53](=[O:65])[NH:54][CH2:55][C:56]1[CH:61]=[CH:60][C:59]([Cl:62])=[CH:58][C:57]=1[CH2:63][NH2:64])([CH3:51])([CH3:50])[CH3:49]>C(Cl)Cl>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][C@H:19]3[C:24](=[O:25])[NH:64][CH2:63][C:57]3[CH:58]=[C:59]([Cl:62])[CH:60]=[CH:61][C:56]=3[CH2:55][NH:54][C:53]([O:52][C:48]([CH3:51])([CH3:49])[CH3:50])=[O:65])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1502080(3S)-4-{[(9H-Fluoren-9-yl)methoxy]carbonyl}morpholine-3-carboxylic acidHCID 11149921Tert-butyl 2-(aminomethyl)-4-chlorobenzylcarbamate

Product 1

HCID 89835594HCID 89835594, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-4-[{(9H-Fluoren-9-yl)methoxy}carbonyl]morpholine-3-carboxylic acid (2.96 g, 8.39 mmol, 1.0 eq) in CH2Cl2 (10 mL), EDCI (3.20 g, 16.68 mmol, 2 eq.), HOBT (2.20 g, 16.28 mmol) and tert-butyl[2-(aminomethyl)-4-chlorobenzyl]carbamate (2.20 g, 8.39 mmol) were added at 0° C. The resulting mixture was stirred for 5 h at room temperature. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed sequentially with saturated NaHCO3 solution (20 mL) and 0.5 M aqueous HCl (20 mL). The organic layer was separated, washed with brine solution (20 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; eluent: 40% EtOAc/hexanes) to afford the title compound as pale yellow semi solid (4.10 g)

Workup

  1. washwashed sequentially with saturated NaHCO3 solution (20 mL) and 0.5 M aqueous HCl (20 mL)
  2. customThe organic layer was separated
  3. washwashed with brine solution (20 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel; eluent: 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d6efba0d00d541d882f52c38c209bb2e
Source dataset
uspto-grants-2015_09
Patent number
US09133147B2

Reaction notes

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